(3-Amino-4-benzyloxyphenyl)acetonitrile → 5-(2-Aminoethyl)-2-benzyloxyaniline

HRID 1032516Notes

Reaction equation

HRID 1032516 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]#[N:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Ni].N>[NH2:18][CH2:17][CH2:16][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([CH:3]=1)[NH2:1]

Participants

4

Reactant 1

HCID 22165986(3-Amino-4-benzyloxyphenyl)acetonitrile

Product 1

HCID 221659935-(2-Aminoethyl)-2-benzyloxyanilineYield 70.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

In the presence of Raney nickel, 9.5 g of (3-amino-4-benzyloxyphenyl)acetonitrile is hydrogenated in 60 ml of ammonia-saturated methanol at 100° C. and under a pressure of 5,000 kPa. The hydrogenation product is chromatographed on silica gel with methylene chloride/methanol (7:3), thus obtaining 6.82 g of 5-(2-aminoethyl)-2-benzyloxyaniline as an oil, converted by treatment with 2N HCl in methanol and evaporation into the hydrochloride.

Workup

  1. customThe hydrogenation product is chromatographed on silica gel with methylene chloride/methanol (7:3)

Sources & evidence

ORD record
ord-8cff01d4ad3a4265bf4ac09ff41cea2a
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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